HRP20240283T1 - Derivati 4-fluoro-1h-pirazolo[3,4-c]piridina kao selektivni inhibitori brutonove tirozin kinaze (btk) za liječenje b-staničnih limfoma i autoimunih bolesti - Google Patents
Derivati 4-fluoro-1h-pirazolo[3,4-c]piridina kao selektivni inhibitori brutonove tirozin kinaze (btk) za liječenje b-staničnih limfoma i autoimunih bolesti Download PDFInfo
- Publication number
- HRP20240283T1 HRP20240283T1 HRP20240283TT HRP20240283T HRP20240283T1 HR P20240283 T1 HRP20240283 T1 HR P20240283T1 HR P20240283T T HRP20240283T T HR P20240283TT HR P20240283 T HRP20240283 T HR P20240283T HR P20240283 T1 HRP20240283 T1 HR P20240283T1
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Links
- 208000023275 Autoimmune disease Diseases 0.000 title claims 2
- KHJBNXJABVZOQK-UHFFFAOYSA-N 4-fluoro-1h-pyrazolo[3,4-c]pyridine Chemical class FC1=CN=CC2=C1C=NN2 KHJBNXJABVZOQK-UHFFFAOYSA-N 0.000 title 1
- 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 title 1
- 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 title 1
- 208000003950 B-cell lymphoma Diseases 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000005936 piperidyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 229940124291 BTK inhibitor Drugs 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (15)
1. Spoj prikazan kao formula (I), njegov stereoizomer ili njegova farmaceutski prihvatljiva sol,
[image]
pri čemu,
T1 je neovisno izabran od N i CH;
R2 je neovisno izabran od H, C1-6 alkila, C2-6 alkenila i C2-6 alkinila, pri čemu, svaki C1-6 alkil, C2-6 alkenil i C2-6 alkinil je neovisno i izborno supstituiran sa 1, 2 ili 3 Ra;
prsten A je izabran od fenila i heteroarila sa 5 do 6 članova;
M je neovisno izabran od C3-6 cikloalkila i heterocikloalkila sa 3 do 6 članova, pri čemu, svaki C3-6 cikloalkil i heterocikloalkil sa 3 do 6 članova je neovisno i izborno supstituiran sa 1, 2 ili 3 Rb;
svaki R1 i R3 je neovisno izabran od F, Cl, Br, I, OH, NH2, CN;
svaki n i m je neovisno izabran od 0, 1, 2 ili 3, i n i m nisu istovremeno 0;
svaki L1 i L2 je neovisno izabran od -CH2-, -CH2CH2-, -O-, -C(=O)- i - C(=O)-NH-;
Ra je neovisno izabran od H, F, Cl, Br, I, OH, NH2, CN, C1-3 alkila, C1-3 alkoksi i C1-3 alkilamino, pri čemu, svaki C1-3 alkil, C1-3 alkoksi i C1-3 alkilamino je neovisno i izborno supstituiran sa 1, 2 ili 3 R;
Rb je izabran od F, Cl, Br, I, CH3;
R je izabran od H, F, Cl, Br, I;
svaki heteroaril sa 5 do 6 članova i heterocikloalkil sa 3 do 6 članova neovisno sadrži 1, 2, 3 ili 4 heteroatoma ili grupa heteroatoma neovisno izabranih od -NH-, -O-, -S-, -C(=O)-, -S(=O)- i N.
2. Spoj prikazan kao formula (I) prema patentnom zahtjevu 1, naznačen time što je Ra neovisno izabran od H, F, Cl, Br, I, OH, NH2, CN, CH3, OCH3, NH(CH3) i N(CH3)2.
3. Spoj prikazan kao formula (I) prema patentnom zahtjevu 2, naznačen time što je R2 neovisno izabran od H, C1-3 alkila, C2-4 alkenila i C2-4 alkinila, i, svaki C1-3 alkil, C2-4 alkenil i C2-4 alkinil je neovisno i izborno supstituiran sa 1, 2 ili 3 Ra.
4. Spoj prikazan kao formula (I) prema patentnom zahtjevu 3, naznačen time što je R2 neovisno izabran od H, CH3, vinila i propinila.
5. Spoj prikazan kao formula (I) prema patentnom zahtjevu 1, naznačen time što je M neovisno izabran od ciklopropila, ciklobutila, ciklopentila, cikloheksila, azetidinila, oksetanila, piperidila i morfolinila, i, svaki ciklopropil, ciklobutil, ciklopentil, cikloheksil, azetidinil, oksetanil, piperidil i morfolinil je neovisno i izborno supstituiran sa 1, 2 ili 3 Rb.
6. Spoj prikazan kao formula (I) prema patentnom zahtjevu 5, naznačen time što je M neovisno izabran od piperidila i morfolinila.
7. Spoj prikazan kao formula (I) prema patentnom zahtjevu 1, pri čemu,
L1 je izabran od -O- i -C(=O)-NH-;
i/ili, L2 je izabran od -C(=O)- i -C(=O)-NH-;
i/ili, prsten A je izabran od fenila i piridila.
8. Spoj prikazan kao formula (I) prema patentnom zahtjevu 1, pri čemu je strukturna jedinica
[image]
izabrana od
[image]
i
[image]
9. Spoj prikazan kao formula (I) prema patentnom zahtjevu 8, pri čemu je strukturna jedinica
[image]
izabrana od
[image]
i
[image]
10. Spoj prikazan kao formula (I) prema bilo kojem od patentnih zahtjeva 1-7, izabran od:
[image]
naznačen time što,
R1 i R3 su kao što su definirani u patentnom zahtjevu 1;
svaki n i m je neovisno izabran od 0, 1, 2 ili 3, i n i m nisu istovremeno 0;
R2 je kao što je definiran u bilo kojem od patentnih zahtjeva 1, 3 ili 4;
L1 i L2 su kao što su definirani u patentnom zahtjevu 1 ili 7.
11. Spoj prikazan kao formula (I) prema patentnom zahtjevu 10, izabran od:
[image]
[image]
naznačen time što
n, m, R1, R2, R3, L1, L2 su kao što su definirani u patentnom zahtjevu 10.
12. Spoj prikazan kao formula (I) prema bilo kojem od patentnih zahtjeva 1-11, izabran od:
[image]
[image]
13. Spoj prema patentnom zahtjevu 12, izabran od:
[image]
[image]
[image]
14. Farmaceutski pripravak koji sadrži terapeutski efikasnu količinu spoja prema bilo kojem od patentnih zahtjeva 1-13 kao aktivni sastojak, i farmaceutski prihvatljiv nosač.
15. Spoj prema bilo kojem od patentnih zahtjeva 1-13 ili farmaceutski pripravak prema patentnom zahtjevu 14, za uporabu kao lijek srodan BTK inhibitorima; lijek srodan BTK inhibitorima je izborno lijek za liječenje hematološkog tumora i autoimune bolesti; bolest je izborno difuzni B-krupnostanični limfom.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910919180 | 2019-09-26 | ||
CN202010330226 | 2020-04-24 | ||
EP20867917.5A EP4036095B1 (en) | 2019-09-26 | 2020-09-25 | 4-fluoro-1h-pyrazolo[3,4-c]pyridine derivatives as selective bruton's tyrosine kinase (btk) inhibitors for the treatment of b-cell lymphoma and autoimmune diseases |
PCT/CN2020/117690 WO2021057893A1 (zh) | 2019-09-26 | 2020-09-25 | 作为选择性btk激酶抑制剂的吡唑并吡啶类化合物 |
Publications (1)
Publication Number | Publication Date |
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HRP20240283T1 true HRP20240283T1 (hr) | 2024-05-10 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HRP20240283TT HRP20240283T1 (hr) | 2019-09-26 | 2020-09-25 | Derivati 4-fluoro-1h-pirazolo[3,4-c]piridina kao selektivni inhibitori brutonove tirozin kinaze (btk) za liječenje b-staničnih limfoma i autoimunih bolesti |
Country Status (18)
Country | Link |
---|---|
US (1) | US11739090B2 (hr) |
EP (1) | EP4036095B1 (hr) |
JP (1) | JP7213604B2 (hr) |
KR (1) | KR102500569B1 (hr) |
CN (1) | CN114450289B (hr) |
AU (1) | AU2020355845B2 (hr) |
BR (1) | BR112022005729A2 (hr) |
CA (1) | CA3152587C (hr) |
DK (1) | DK4036095T3 (hr) |
FI (1) | FI4036095T3 (hr) |
HR (1) | HRP20240283T1 (hr) |
LT (1) | LT4036095T (hr) |
MX (1) | MX2022003707A (hr) |
PL (1) | PL4036095T3 (hr) |
PT (1) | PT4036095T (hr) |
RS (1) | RS65239B1 (hr) |
SI (1) | SI4036095T1 (hr) |
WO (1) | WO2021057893A1 (hr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20230154243A (ko) * | 2021-03-23 | 2023-11-07 | 점보 드러그 뱅크 컴퍼니 리미티드 | 불소-치환된 피리도피라졸계 화합물의 결정형 및 이의 제조 방법 |
WO2024022234A1 (zh) * | 2022-07-28 | 2024-02-01 | 成都嘉葆药银医药科技有限公司 | 吡唑并吡啶类化合物在制备治疗包括中枢神经系统疾病的btk相关疾病的药物中的用途 |
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SG10201508035TA (en) * | 2007-03-28 | 2015-10-29 | Pharmacyclics Inc | Inhibitors of bruton's tyrosine kinase |
US20150152115A1 (en) * | 2007-12-27 | 2015-06-04 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
KR20120116387A (ko) | 2009-08-27 | 2012-10-22 | 폴리머스 씨알씨 리미티드 | 나노 은-산화아연 조성물 |
EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
CN103848810A (zh) * | 2012-11-30 | 2014-06-11 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
WO2014113942A1 (en) * | 2013-01-23 | 2014-07-31 | Merck Sharp & Dohme Corp. | Btk inhibitors |
WO2014199171A1 (en) * | 2013-06-12 | 2014-12-18 | Proximagen Limited | New therapeutic uses of enzyme inhibitors |
EP3082811B1 (en) * | 2013-12-20 | 2020-01-15 | Merck Sharp & Dohme Corp. | Btk inhibitors |
WO2015095099A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Btk inhibitors |
CN105017256A (zh) * | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | 多氟化合物作为布鲁顿酪氨酸激酶抑制剂 |
CN105085474B (zh) * | 2014-05-07 | 2018-05-18 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
CN105399756B (zh) | 2014-09-05 | 2019-06-25 | 广东东阳光药业有限公司 | Btk抑制剂及其用途 |
WO2016106627A1 (en) * | 2014-12-31 | 2016-07-07 | Merck Sharp & Dohme Corp. | Btk inhibitors |
WO2016106652A1 (en) * | 2014-12-31 | 2016-07-07 | Merck Sharp & Dohme Corp. | Biarylether imidazopyrazine btk inhibitors |
TW201718572A (zh) * | 2015-06-24 | 2017-06-01 | 普林斯匹亞生物製藥公司 | 酪胺酸激酶抑制劑 |
CN105753863B (zh) * | 2015-09-11 | 2018-07-31 | 东莞市真兴贝特医药技术有限公司 | 氧代二氢咪唑并吡啶类化合物及其应用 |
US10662187B2 (en) | 2016-01-21 | 2020-05-26 | Zibo Biopolar Changsheng Pharmaceutical Co. Ltd. | Bruton's tyrosine kinase inhibitors |
CN109071455B (zh) | 2016-03-11 | 2022-08-02 | 嘉兴和剂药业有限公司 | 用于调节布鲁顿酪氨酸激酶的化合物及方法 |
CN109851620B (zh) * | 2016-08-17 | 2020-08-07 | 深圳市塔吉瑞生物医药有限公司 | 用于抑制酪氨酸激酶活性的稠合双环类化合物 |
JOP20190113A1 (ar) | 2016-11-18 | 2019-05-15 | Biocad Joint Stock Co | مثبطات بروتون تيروزين كيناز |
CN106588937B (zh) * | 2017-01-16 | 2018-09-21 | 东莞市真兴贝特医药技术有限公司 | 咪唑并吡嗪类化合物及其制备方法和应用 |
CN110272416A (zh) | 2018-03-14 | 2019-09-24 | 武汉宇科源医药生物科技有限公司 | 吡唑并[3,4-c]吡啶-7-胺衍生物及其制备方法和应用 |
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2020
- 2020-09-25 MX MX2022003707A patent/MX2022003707A/es unknown
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- 2020-09-25 KR KR1020227013965A patent/KR102500569B1/ko active IP Right Grant
- 2020-09-25 FI FIEP20867917.5T patent/FI4036095T3/fi active
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- 2020-09-25 CA CA3152587A patent/CA3152587C/en active Active
- 2020-09-25 LT LTEPPCT/CN2020/117690T patent/LT4036095T/lt unknown
- 2020-09-25 WO PCT/CN2020/117690 patent/WO2021057893A1/zh active Application Filing
- 2020-09-25 EP EP20867917.5A patent/EP4036095B1/en active Active
- 2020-09-25 CN CN202080068213.1A patent/CN114450289B/zh active Active
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- 2020-09-25 SI SI202030375T patent/SI4036095T1/sl unknown
- 2020-09-25 US US17/763,732 patent/US11739090B2/en active Active
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Also Published As
Publication number | Publication date |
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EP4036095A1 (en) | 2022-08-03 |
US11739090B2 (en) | 2023-08-29 |
JP2022542196A (ja) | 2022-09-29 |
CN114450289A (zh) | 2022-05-06 |
US20220324864A1 (en) | 2022-10-13 |
EP4036095B1 (en) | 2024-01-31 |
AU2020355845B2 (en) | 2023-04-06 |
CN114450289B (zh) | 2024-01-02 |
KR20220061262A (ko) | 2022-05-12 |
PT4036095T (pt) | 2024-02-19 |
KR102500569B1 (ko) | 2023-02-16 |
AU2020355845A1 (en) | 2022-05-19 |
FI4036095T3 (fi) | 2024-02-14 |
LT4036095T (lt) | 2024-03-25 |
EP4036095A4 (en) | 2022-12-07 |
BR112022005729A2 (pt) | 2022-06-21 |
WO2021057893A1 (zh) | 2021-04-01 |
RS65239B1 (sr) | 2024-03-29 |
CA3152587C (en) | 2023-05-23 |
SI4036095T1 (sl) | 2024-04-30 |
PL4036095T3 (pl) | 2024-04-15 |
DK4036095T3 (da) | 2024-03-04 |
MX2022003707A (es) | 2022-06-23 |
JP7213604B2 (ja) | 2023-01-27 |
CA3152587A1 (en) | 2021-04-01 |
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